Fluazinam (Ref: IKF 1216)

Fluazinam (Ref: IKF 1216)	Last updated: 26/01/2021
(Also known as: B 1216; CHA-580; MCW)

GENERAL INFORMATION

Description

A protective broad spectrum fungicide used to control various soil-borne fungal pathogens on a range of crops. It also has some acaricidal activity.

Example pests controlled

Sclerotinia blight, Late blight, White mould, Clubroot, Downy mildew, Scab, Alternaria blotch, Mites

Example applications

Peanuts; Potatoes; Grape vines; Fruit including citrus and apples; Crucifers

Efficacy & activity

Efficiacy evaluated and proved in field trials and extensive use.

Availability status

Current

Introduction & key dates

1990, first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

28/02/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria/Denmark

Date EC 1107/2009 inclusion expires

28/02/2021

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓		✓	✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓		✓	✓	✓	✓	✓	✓	✓

Also used in

Australia

Chemical structure

Isomerism

Chemical formula

C₁₃H₄Cl₂F₆N₄O₄

Canonical SMILES

C1=C(C=NC(=C1Cl)NC2=C(C=C(C(=C2[N+](=O)[O-])Cl)C(F)(F)F)[N+](=O)[O-])C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UZCGKGPEKUCDTF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fluazinam	-

General status

Pesticide type

Fungicide, Acaricide

Substance group

Phenylpyridinamine

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU 2019 dossier: 5-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-4,6-dinitro-o-toluidine < 2.0g kg⁻¹

Substance origin

Synthetic

Mode of action

Protective action with some residual effects. Uncoupler of oxidative phosphorylation

CAS RN

79622-59-6

EC number

CIPAC number

521

US EPA chemical code

129098

PubChem CID

91731

Molecular mass

465.14

PIN (Preferred Identification Name)

3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)pyridin-2-amine

IUPAC name

3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-2,6-dinitro-p-toluidine

CAS name

3-chloro-N-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2-pyridinamine

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

Pale yellow crystals

Related substances & organisms

metalaxyl-M

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Shirlan
Tizca
Volley

Example products using this active

AgriGuard
Headland
Landgold
Makhteshim-Agan
Syngenta

Formulation and application details

Often supplied as a soluble concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.135

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

8000

n-Hexane

192000

Methanol

451000

Toluene

853000

Acetone

Melting point (°C)

117

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

7.41 X 10⁰⁴

Calculated

Log P

4.87

at 22 °C

High

Bulk density (g ml⁻¹)

1.81

Dissociation constant pKa) at 25 °C

7.22

Weak acid

Vapour pressure at 20 °C (mPa)

0.0172

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

5.93 X 10^-02

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Acidic pH: 244nm=20837
Neutral pH: 265nm=16163, 347nm=15140, 480nm=2605
Basic pH: 265nm=1700, 347nm=19256, 480nm=3628

Surface tension (mN m⁻¹)

66.3

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

124

Persistent

DT₅₀ (lab at 20 °C)

124

Persistent

DT₅₀ (field)

25.9

Non-persistent

DT₉₀ (lab at 20 °C)

359

Persistent

DT₉₀ (field)

104.5

DT₅₀ modelling endpoint

Note

EU 2019 dossier lab studies DT₅₀ (normalised) range 12.7-527 days, DT₉₀ (measured) range 62.2->1000 days, Soils=10, Field studies DT₅₀ (normalised) range 20.7-34.3 days, DT₉₀ (measured) range 44.8-145 days, Soils=4 Other studies: DT₅₀ (1) Lab range 37-224 days, field range 6-15 days (B5), (2) 29 days (DW4)

Dissipation rate RL₅₀ on plant matrix

Value

4.3

Note

Grape berries, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.1

Moderately fast

Note

Degradation in daylight, stable in the dark

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

8.7

Non-persistent

Note

pH sensitive: stable at pH 4, DT₅₀ 4.7 days at pH 9

Water-sediment DT₅₀ (days)

4.5

Fast

Water phase only DT₅₀ (days)

4.5

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

220

Non-mobile

K_oc

16430

Notes and range

EU 2019 dossier K_d range 126-264 mL g⁻¹, K_oc range 10245-26250 mL g⁻¹, Soils=4

Freundlich

K_f

26.6

Slightly mobile

K_foc

1958

¹/_n

0.65

Notes and range

EU 2019 dossier K_f range 11.12-43.48 mL g⁻¹, K_foc range 1705-2316 mL g⁻¹, ¹/_n range 0.6204-0.6813, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.00

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

1.90 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

5-((3-chloro-5-(trifluoromethyl)-2-pyridyl)amino)-alpha,alpha,alpha-trifluoro-4,6-dinitro-o-cresol

Soil

0.136

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-chloro-6-(3-chloro-5-trifluoromethyl-2-pyridylamino)-α,α,α--trifluoro-5-nitro-m-toluidine

MAPA; G-525

Animal; Water; Sediment; Soil

4-chloro-6-(3-chloro-5-trifluoromethyl-2-pyridylamino)-α,α,α-trifluoro-5-nitro-m-toluidine

AMPA-Fluazinam; AMPA; AMPFA

Plant; Soil; Sediment

4-chloro-2-(3-chloro-5-trifluoromethyl-2-pyridylamino)-5-trifluoromethyl-m-phenylenediamine

DAPA

Plant; Soil; Animal

5-Chloro-6-(3-chloro-2,6-dinitro-4-trifluoromethylanilino)nicotinic acid

CAPA

Soil; Surface water; Sediment

trifluoroacetic acid

TFAA

Plant

3-[[4-amino-3-[[3-chloro-5-trifluoromethyl)-2-pyridyl]amino]- α,α,α-trifluoro-6-nitro-o-tolyl]thio]-2-(β-D-glucopyranosyloxy)

AMGT

Plant

4,9-dichloro-6-nitro-8-(trifluoromethyl)-pyrido-[1,2-a]benzimidazole-2-carboxylic acid

G504

Surface water

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1018

Threshold for concern

CT₅₀ (days)

6.0

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 4100

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 3.48

Dog

High

(ppm diet)

> 1.0

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

7.26

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

1782

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1230 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

23.6

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.035

Oncorhynchus mykisss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00069

Pimephales promelas

High

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.22

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.01

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0414

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.00327

Chironomus riparius emergence

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

53.6

Lemna gibba

Low

Non-target plants

> 1500

Cucumber
Vegetative vigour, ER₅₀
as g ha⁻¹

> 1500

Cucumber
Seedling emergence, ER₅₀
as g ha⁻¹

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.16

Pseudokirchneriella subcapitata 96 hour

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

> 0.007

Raphidocelis subcapitata

Moderate

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Bombus terrestris

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 257

Bombus terrestris

Low

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 400

Osmia bicornis

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

55.8

Osmia bicornis

Moderate

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

< 0.175

Eisenia andrei corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Eisenia foetida corr

Chronic NOEC (mg kg⁻¹)

0.615

Folsomia candida,corr

Other arthropod (1)

LR₅₀ g ha⁻¹

2500

Mortality
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

34.3

Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.684 mg Fluazinam 500SC/kg 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.01

Zooplankton

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 4100

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.1

Rat 4 hr (nose only dust aerosol)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.01

Mouse SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.07

Rabbit SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

0.025

Rabbit SF=100

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.004

Dog SF=100

Dermal penetration studies (%)

0.3-5.0

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Low to moderate risks identified for bystanders and residents mainly from spray drift

Occupational

Acceptable risk for operators for proposed uses with PPE/PPC
Acceptable risk for other farm workers for proposed uses

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Potential liver toxicant
May cause allergic contact dermatitis and occupational asthma
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317, H318, H332, H361d
Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R63
T - Toxic: R23
Xn - Harmful: R41, R43
N - Dangerous for the environment: R53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fluazinam

French

fluazinam

German

Fluazinam

Danish

fluazinam

Italian

fluazinam

Spanish

fluazinam

Greek

Polish

fluazynam

Swedish

fluazinam

Hungarian

fluazinam

Dutch

Record last updated:	26/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242